In escrow on my first purchase – seeking council

[Robert DuBois]

Hi everyone,

I'm in contract to buy an 80-year-old $790k home in Santa Cruz, CA (listing was $90k over this). Property has an un-permitted ADU. I plan to rent both units. This would be my first property.

I'm looking for: 
a) sage advice from those more experienced than I am, and
b) to know what questions you would be asking in this scenario

Backstory:
I'm estimating the mthly PITI will be around $4400/mth, plus another $1000-$1200/mth for repairs, vacancies, legal, etc. That puts me at $5400-$5600 I'll need per month, and I've been testing the rental market and think I can get at least $5400.

In exchange for getting into my first house and building wealth long term I'm willing to cover $100-$200/mth out of my own pocket. 

On paper it's not a killer deal, but this is a tough market and I'm looking at it as a buy-and-hold. I'm trying to get into the market rather than sit on the sidelines, but my biggest fear is getting trapped in a big mortgage only to watch the value of my home fall. 

Thanks kindly,

Robert